The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benzylation, and Cyclization Reactions

A convenient and practical pathway to 2-cyano and 2-ester anilines is described via efficient and selective copper(II)-catalyzed reductive amination via hydrosilylation process. Both 2-cyano and 2-ester anilines were successfully synthesized with good functional group tolerance and high selectivity. The application of the 2-cyano and -iodine containing anilines was developed in the synthesis of indoloindole derivatives via CuSO4-catalyzed N-benzylation and cyclization reaction in 'one pot'. More interestingly, the photophysical property investigations of these 2-cyano and 2-ester containing anilines exhibit excellent fluorescent properties, which have great potential application in the development of interesting near-ultraviolet optical devices in the near future.

Automated summary

This study describes a convenient and practical method for the synthesis of 2-cyano and 2-ester anilines via efficient and selective copper-catalyzed reductive amination. These compounds were successfully synthesized with good functional group tolerance. Furthermore, the synthesized compounds exhibited excellent fluorescent properties, which may have potential applications in the development of near-ultraviolet optical devices.